Hydroxylamine → HCID 86641002, compound

HRID 422860Notes

Reaction equation

HRID 422860 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.[NH2:31][OH:32]>CS(C)=O.O>[OH:32][N:31]=[C:27]([C:26]1[CH:29]=[CH:30][C:23]([CH2:22][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]3([CH2:14][O:13][C:12]4[CH:15]=[C:16]5[C:20](=[CH:21][C:11]3=4)[CH2:19][CH2:18][O:17]5)[C:2]2=[O:1])=[CH:24][CH:25]=1)[NH2:28]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 59352617HCID 59352617, compound

Product 1

HCID 86641002HCID 86641002, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzonitrile (1.30 g, 32.9 mmol) in dimethyl sulfoxide (10 mL) was added 50% wt solution hydroxylamine in water (2 mL). The reaction was heated with stirring at 80° C. for 1 h, then cooled to ambient temperature and the product was precipitated by adding distilled water (25 mL). The solid was filtered and air dried to afford N′-hydroxy-4-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzenecarboximidamide (1.32 g, 93%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 9.17 (s, 1H), 7.40-7.03 (m, 13H), 6.99-6.92 (m, 2H), 6.79-6.74 (m, 2H), 6.58-6.50 (m, 1H), 5.10 (s, 1H); MS (ES−) m/z 468.2, 470.2 (M−1).

Workup

  1. temperatureThe reaction was heated
  2. temperaturecooled to ambient temperature
  3. customthe product was precipitated
  4. additionby adding
  5. distillationdistilled water (25 mL)
  6. filtrationThe solid was filtered
  7. customair dried

Sources & evidence

ORD record
ord-d300acfea9524b5bb4ea21c39d1d3431
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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